u/dev_nik

Been looking into WP-to-headless migrations (Sanity/Strapi + Next.js) lately and the thing that keeps coming up as the biggest time sink isn't the content migration itself, it's redirect mapping. Years of slug history with duplicates, chains, and loops apparently eats way more time than anyone budgets for.

A couple other things I've seen bite people:

• Preview workflow parity for content editors (WP's preview-on-save is apparently sorely missed post-migration)
• SEO metadata (og:title etc.) not migrating cleanly, causing ranking dips that only get noticed days later

For those who've done this migration for a client or your own site: how did you handle the redirect mapping specifically? Custom script, existing tool, manual spreadsheet triage? Curious what's actually worked vs. what ate more time than expected.

Curious if others have hit this: a plugin conflict (or combo of plugins) that broke something so badly - site down, client furious, hours lost debugging - that it made you seriously consider whether WordPress was even the right long-term foundation for that project.

Not looking to bash WP, I still use it for plenty of stuff. But I've had a couple of cases lately where the fix took longer than it would've taken to just... not have that problem in the first place. Page builder conflicts, two SEO plugins fighting over meta tags, that kind of thing.

What's the worst plugin conflict you've dealt with, and did it change how you approach a site's stack afterward?